How to Make the Sinatra Smash Cocktail

You’ll get a kick out of the Ol’ Blue Eyes–inspired Sinatra Smash.

At a time when celebrity endorsements are a matter of complicated financial terms and stacks of legal agreements, the story of Frank Sinatra and Jack Daniel’s is difficult to imagine. Sinatra liked Jack Daniel’s, and that was enough. Long before the relationship was formalized, the singer was happily drinking and promoting the brand (he liked it so much, in fact, that he’s buried with a bottle), and Wynn honors Sinatra’s devotion with a signature cocktail called the Sinatra Smash.

“Jack Daniel’s—that’s a good place to start.” This was the advice passed on to Sinatra from Jackie Gleason when the crooner, worried about a dame, said he wanted a “serious drink,” and it’s a good place to start for the Sinatra Smash. A serious base of Gentleman Jack ensures that the whiskey flavor holds up to the added fresh blackberries, black currant liqueur, house-infused vanilla simple syrup, and sweet-and-sour mix. “It really is one of the drinks that people know about in Vegas, and people come in specifically for it,” says Wynn property mixologist Damian Cross. “Though the drink started at Sinatra restaurant, it’s now available at all of the bars at Wynn and Encore.”

Ol’ Blue Eyes preferred his Jack Daniel’s on ice with a splash of water. Wynn has three varieties of the whiskey available: the classic Jack Daniel’s Old No. 7; Gentleman Jack, which is a smoother version of the classic; and Sinatra Select, which is aged in specially grooved barrels that provide more surface area, producing a spicier, smokier flavor. Sinatra Select is also bottled at 90 proof, which is closer to what Sinatra would have been drinking back in the day. (Since then, Jack Daniel’s has changed the formulation of Old No. 7 to be 80 proof and less in need of that splash of water.) As Cross says, “Jack Daniel’s, Frank Sinatra, and Steve Wynn—it’s all of the legends coming together.”

SINATRA SMASH

5 fresh blackberries
1 1∕2 oz. fresh sweet-and-sour mix
1∕4 oz. vanilla-infused simple syrup
3∕4 oz. crème de cassis
2 oz. Gentleman Jack Tennessee whiskey

Muddle 3 of the blackberries in a shaker. Add ice, shake for 8 seconds, then strain into a rocks glass filled with crushed ice. Garnish with the remaining 2 blackberries.